Methanol → HCID 58171618, compound

HRID 1752305Notes

Reaction equation

HRID 1752305 reaction equation
[Na].[CH2:2]([N:9]1[CH2:13][CH2:12][CH:11]([C:14]2[N:19]=[CH:18][C:17](Br)=[CH:16][N:15]=2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:21][OH:22]>>[CH2:2]([N:9]1[CH2:13][CH2:12][CH:11]([C:14]2[N:19]=[CH:18][C:17]([O:22][CH3:21])=[CH:16][N:15]=2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 58171611HCID 58171611, compound

Product 1

HCID 58171618HCID 58171618, compoundYield 27.2%

Conditions

Temperature
110 °C

Procedure

Sodium (362 mg, 15.75 mmol) was added portionwise to methanol (15 mL) at 22° C. until a homogeneous solution was obtained. The solution was then treated with 2-(1-benzyl-pyrrolidin-3-yl)-5-bromo-pyrimidine (1 g, 3.15 mmol) and heated in a sealed tube at 110° C. for 24 h. The mixture was cooled, concentrated in vacuo. The residue was purified by column chromatography to afford 2-(1-benzylpyrrolidin-3-yl)-5-methoxypyrimidine (230 mg 27.2%) as a yellow oil.

Workup

  1. customwas obtained
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-188733e1bf5e4cd5908d69dbebb01783
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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